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    • 1. 发明授权
    • Method for producing long-chain glycine-N,N-diacetic acid derivatives
    • 制备长链甘氨酸-N,N-二乙酸衍生物的方法
    • US06307086B1
    • 2001-10-23
    • US09463998
    • 2000-03-21
    • Rainer RahmThomas GreindlAlfred OftringGuenter OetterJuergen DeteringGerold Braun
    • Rainer RahmThomas GreindlAlfred OftringGuenter OetterJuergen DeteringGerold Braun
    • C07C25300
    • C07C229/08C07C229/16C07C253/00C07C255/25
    • A process for preparing compounds of the formula IIb  where R is C6-C30-alkyl or C6-C30-alkenyl, which may additionally have upto 5 hydroxyl groups, formyl groups, C1-C4-alkoxy groups, phenoxy groups or C1-C4-alkoxycarbonyl groups as substituents and may be interrupted by upto 5 nonadjacent oxygen atoms, or alkoxylate groups of the formula —(CH2)k—O—(A1O)m—(A2O)n—Y where A1 and A2 are, independently of one another, 1,2-alkylene groups having 2 to 4 carbon atoms, Y is hydrogen, C1-C12-alkyl, phenyl or C1-C4-alkoxycarbonyl, and k is 1, 2 or 3, and m and n are each numbers from 0 to 50, and the total of m+n must be at least 4, by reacting iminodiacetonitrile with aldehydes of the formula R—CHO and HCN or alkali metal cyanides, the process being carried out a) in the absence of an organic solvent and in the presence of a Lewis or Brönsted acid, or b) in the presence or absence of an organic solvent and in the presence of an emulsifier, or c) in the presence or absence of an organic solvent and under a pressure in the range from 1 to 40 bar.
    • 制备式IIb化合物的方法,其中R是C 6 -C 30 - 烷基或C 6 -C 30烯基,其可另外具有多达5个羟基,甲酰基,C 1 -C 4 - 烷氧基,苯氧基或C 1 -C 4 - 烷氧基羰基作为取代基,并且可以被至多5个不相邻的氧原子间隔或式 - (CH2)kO-(A1O)m-(A2O)nY的烷氧基化物,其中A1和A2彼此独立地为1,2 具有2至4个碳原子的亚烷基,Y是氢,C 1 -C 12 - 烷基,苯基或C 1 -C 4 - 烷氧基羰基,k是1,2或3,m和n各自为0至50, 通过使亚氨基二乙腈与式R-CHO和HCN或碱金属氰化物的醛反应,所述m + n的总和必须至少为4,该方法在不存在有机溶剂的情况下进行,并且在Lewis的存在下 或布朗斯台德酸,环)在存在或不存在有机溶剂的情况下和在乳化剂orc的存在下)在存在或不存在有机溶剂的情况下 在1至40巴的压力范围内。
    • 2. 发明授权
    • Method for producing long-chain glycine-N,N-diacetic acid derivatives
    • 制备长链甘氨酸-N,N-二乙酸衍生物的方法
    • US06420593B2
    • 2002-07-16
    • US09875995
    • 2001-06-08
    • Rainer RahmThomas GreindlAlfred OftringGuenter OetterJuergen DeteringGerold Braun
    • Rainer RahmThomas GreindlAlfred OftringGuenter OetterJuergen DeteringGerold Braun
    • C07C22904
    • C07C229/08C07C229/16C07C253/00C07C255/25
    • A process for preparing compounds of the formula IIb  where R is C6-C30-alkyl or C6-C30-alkenyl, which may additionally have upto 5 hydroxyl groups, formyl groups, C1-C4-alkoxy groups, phenoxy groups or C1-C4-alkoxycarbonyl groups as substituents and may be interrupted by upto 5 nonadjacent oxygen atoms, or alkoxylate groups of the formula —(CH2)k—O—(A1O)m—(A2O)n—Y where A1 and A2 are, independently of one another, 1,2-alkylene groups having 2 to 4 carbon atoms, Y is hydrogen, C1-C12-alkyl, phenyl or C1-C4-alkoxycarbonyl, and k is 1, 2 or 3, and m and n are each numbers from 0 to 50, and the total of m+n must be at least 4, by reacting iminodiacetonitrile with aldehydes of the formula R—CHO and HCN or alkali metal cyanides, the process being carried out a) in the absence of an organic solvent and in the presence of a Lewis or Brönsted acid, or b) in the presence or absence of an organic solvent and in the presence of an emulsifier, or c) in the presence or absence of an organic solvent and under a pressure in the range from 1 to 40 bar.
    • 制备式IIb化合物的方法,其中R是C 6 -C 30 - 烷基或C 6 -C 30烯基,其可另外具有多达5个羟基,甲酰基,C 1 -C 4 - 烷氧基,苯氧基或C 1 -C 4 - 烷氧基羰基作为取代基,并且可以被至多5个不相邻的氧原子间隔或式 - (CH2)kO-(A1O)m-(A2O)nY的烷氧基化物,其中A1和A2彼此独立地为1,2 具有2至4个碳原子的亚烷基,Y是氢,C 1 -C 12 - 烷基,苯基或C 1 -C 4 - 烷氧基羰基,k是1,2或3,m和n各自为0至50, 通过使亚氨基二乙腈与式R-CHO和HCN或碱金属氰化物的醛反应,所述m + n的总和必须至少为4,该方法在不存在有机溶剂的情况下进行,并且在Lewis的存在下 或布朗斯台德酸,环)在存在或不存在有机溶剂的情况下和在乳化剂orc的存在下)在存在或不存在有机溶剂的情况下 在1至40巴的压力范围内。
    • 3. 发明授权
    • Preparation of glycine-N,N-diacetic acid derivatives
    • 甘氨酸-N,N-二乙酸衍生物的制备
    • US5849950A
    • 1998-12-15
    • US653024
    • 1996-05-24
    • Thomas GreindlAlfred OftringGerold BraunJochen WildBirgit Potthoff-KarlGeorg Schuh
    • Thomas GreindlAlfred OftringGerold BraunJochen WildBirgit Potthoff-KarlGeorg Schuh
    • C07C227/18C07C227/26C07C229/16C07C229/00
    • C07C227/26
    • Glycine-N,N-diacetic acid derivatives I ##STR1## where R is unsubstituted or substituted alkyl, alkenyl, alkoxylate groups, phenylalkyl, phenyl, a heterocyclic ring or a radical of the formula ##STR2## where A is an alkylene bridge or a chemical bond, and M is hydrogen, alkali metal, alkaline earth metal, ammonium or substituted ammonium in the appropriate stoichiometric amounts, are prepared by reacting A) corresponding 2-substituted glycines or 2-substituted glycinonitriles or doubled glycines of the formula ##STR3## or doubled glycinonitriles of the formula ##STR4## or precursors of the glycine derivatives named as starting material with formaldehyde and hydrogen cyanide in aqueous medium at a pH of from 0 to 11 or B) iminodiacetonitrile or iminodiacetic acid with appropriate monoaldehydes of the formula R--CHO or dialdehydes of the formula OHC--A--CHO and hydrogen cyanide in aqueous medium at a pH of from 0 to 11 and, where appropriate, subsequent hydrolysis of nitrile functionalities which are present, where the starting material used comprises unpurified raw material derived from the industrial synthesis of glycine derivatives or their precursors or of iminodiacetonitrile or iminodiacetic acid, or mother liquors produced in such syntheses.
    • 甘氨酸-N,N-二乙酸衍生物I(I)其中R是未取代或取代的烷基,烯基,烷氧基化物,苯基烷基,苯基,杂环或下式的基团其中A是亚烷基 桥或化学键,并且M是氢,碱金属,碱土金属,铵或取代的铵以适当的化学计量的量,通过使A)相应的2-取代的甘氨酸或2-取代的甘氨酸腈或式 或者在水性介质中以甲醛和氰化氢命名为起始原料的甘氨酸衍生物的前体(pH值为0至11)或B)亚氨基二乙腈或亚氨基二乙酸与适当的单醛 式R-CHO或式OHC-A-CHO的二醛和氰化氢在水介质中的pH为0至11,并且在适当的情况下随后水解腈官能团 其中使用的起始材料包括衍生自甘氨酸衍生物或其前体或亚氨基乙腈或亚氨基二乙酸的工业合成的未纯化原料,或在这种合成中产生的母液。
    • 6. 发明授权
    • Process for the preparation of aqueous solutions of methylglycine-N,N-diacetic acid trialkali metal salts
    • 制备甲基甘氨酸-N,N-二乙酸三烷基金属盐水溶液的方法
    • US08802894B2
    • 2014-08-12
    • US13431381
    • 2012-03-27
    • Alfred OftringGerold BraunArnulf Lauterbach
    • Alfred OftringGerold BraunArnulf Lauterbach
    • C07C227/18
    • C07C253/00C07C227/26C07C255/25C07C229/12
    • A process for preparing an aqueous solution of a methylglycine-N,N-diacetic acid trialkali metal salt at a high yield and purity by Strecker synthesis, the process including: reacting an aqueous solution containing α-alanine with formaldehyde and hydrocyanic acid, to obtain α-alanine-N,N-diacetonitrile in one reaction unit; and saponification of the α-alanine-N,N-diacetonitrile with a base, to obtain the methylglycine-N,N-diacetic acid trialkali metal salt, wherein the α-alanine is partially neutralized and the addition of formaldehyde and hydrocyanic acid are controlled such that a concentration of free hydrocyanic acid in the liquid reaction mixture at any time is limited such that secondary reactions that produce formaldehyde cyanohydrin, consecutive reactions of formaldehyde cyanohydrin, and the polymerization of hydrocyanic acid, only occur insofar as the specification requirements, such as nitrilotriacetic acid content and color, for methylglycine-N,N-diacetic acid trialkali metal salts are observed.
    • 一种通过Strecker合成以高产率和纯度制备甲基甘氨酸-N,N-二乙酸三烷基金属盐的水溶液的方法,该方法包括:使含有α-丙氨酸的水溶液与甲醛和氢氰酸反应,得到 α-丙氨酸-N,N-二乙腈在一个反应​​单元中; 并用碱对α-丙氨酸-N,N-二乙腈进行皂化,得到甲基甘氨酸-N,N-二乙酸三碱金属盐,其中α-丙氨酸被部分中和,加入甲醛和氢氰酸被控制 使得在任何时候液体反应混合物中的游离氢氰酸的浓度受到限制,使得产生甲醛氰醇的二次反应,甲醛氰醇的连续反应和氢氰酸的聚合仅发生在规范要求的范围内,例如 观察到甲基甘氨酸-N,N-二乙酸三烷基金属盐的次氮基三乙酸含量和颜色。
    • 7. 发明授权
    • Method for producing methylglycine-N,N-diethanoic acid-trialkali metal salts with a low by-product content
    • 具有低副产物含量的甲基甘氨酸-N,N-二乙酸 - 三烷基金属盐的制备方法
    • US07671234B2
    • 2010-03-02
    • US11913597
    • 2006-05-02
    • Alfred OftringGerold BraunFriedrich WirsingArmin StammKai-Uwe Baldenius
    • Alfred OftringGerold BraunFriedrich WirsingArmin StammKai-Uwe Baldenius
    • C07C227/26C07C229/16
    • C07C227/26C07C229/16
    • The invention relates to a process for preparing low-by-product, light-color methylglycine-N,N-diacetic acid tri(alkali metal) salt by alkaline hydrolysis of methylglycinediacetonitrile (MGDN), comprising the steps in the sequence (a) to (f): (a) mixing of MGDN with aqueous alkali at a temperature of ≦30° C.; (b) allowing the aqueous alkaline MGDN suspension to react at a temperature in the range from 10 to 30° C. over a period of from 0.1 to 10 h to form a solution; (c) allowing the solution from step (b) to react at a temperature in the range from 30 to 40° C. over a period of from 0.1 to 10 h; (d) optionally allowing the solution from step (c) to react at a temperature in the range from 50 to 80° C. over a period of from 0.5 to 2 h; (e) optionally allowing the solution from step (c) or (d) to react at a temperature in the range from 110 to 200° C. over a period of from 5 to 60 min; (f) hydrolysis and removal of ammonia of the solution obtained in step (c), (d) or (e) by stripping at a temperature of from 90 to 105° C.
    • 本发明涉及通过甲基甘氨二乙腈(MGDN)的碱水解制备低副产物,浅色甲基甘氨酸-N,N-二乙酸三(碱金属)盐的方法,包括步骤(a)至 (f):(a)在温度为30℃的温度下,将MGDN与碱水溶液混合; (b)使含水碱性MGDN悬浮液在10至30℃的温度下反应0.1至10小时以形成溶液; (c)允许来自步骤(b)的溶液在0.1至10小时的时间内在30至40℃的温度下反应; (d)任选地允许步骤(c)的溶液在0.5至2小时的时间内在50至80℃的温度下反应; (e)任选地允许来自步骤(c)或(d)的溶液在110至200℃的温度下在5至60分钟的时间内反应; (f)通过在90至105℃的温度下汽提来水解和除去在步骤(c),(d)或(e)中获得的溶液中的氨。
    • 8. 发明申请
    • Method For Producing Methylglycine-N,N-Diethanoic Acid-Trialkali Metal Salts With A Low By-Product Content
    • 生产含有低副产物含量的甲基甘氨酸-N,N-二氢化萘 - 三碱金属盐的方法
    • US20080194873A1
    • 2008-08-14
    • US11913597
    • 2006-05-02
    • Alfred OftringGerold BraunFriedrich WirsingArmin StammKai-Uwe Baldenius
    • Alfred OftringGerold BraunFriedrich WirsingArmin StammKai-Uwe Baldenius
    • C07C229/24
    • C07C227/26C07C229/16
    • The invention relates to a process for preparing low-by-product, light-color methylglycine-N,N-diacetic acid tri(alkali metal) salt by alkaline hydrolysis of methylglycinediacetonitrile (MGDN), comprising the steps in the sequence (a) to (f): (a) mixing of MGDN with aqueous alkali at a temperature of ≦30° C.; (b) allowing the aqueous alkaline MGDN suspension to react at a temperature in the range from 10 to 30° C. over a period of from 0.1 to 10 h to form a solution; (c) allowing the solution from step (b) to react at a temperature in the range from 30 to 40° C. over a period of from 0.1 to 10 h; (d) optionally allowing the solution from step (c) to react at a temperature in the range from 50 to 80° C. over a period of from 0.5 to 2 h; (e) optionally allowing the solution from step (c) or (d) to react at a temperature in the range from 110 to 200° C. over a period of from 5 to 60 min; (f) hydrolysis and removal of ammonia of the solution obtained in step (c), (d) or (e) by stripping at a temperature of from 90 to 105° C.
    • 本发明涉及通过甲基甘氨二乙腈(MGDN)的碱水解制备低副产物,浅色甲基甘氨酸-N,N-二乙酸三(碱金属)盐的方法,包括步骤(a)至 (f):(a)在<= 30℃的温度下将MGDN与碱水溶液混合; (b)使含水碱性MGDN悬浮液在10至30℃的温度下反应0.1至10小时以形成溶液; (c)允许来自步骤(b)的溶液在0.1至10小时的时间内在30至40℃的温度下反应; (d)任选地允许步骤(c)的溶液在0.5至2小时的时间内在50至80℃的温度下反应; (e)任选地允许来自步骤(c)或(d)的溶液在110至200℃的温度下在5至60分钟的时间内反应; (f)通过在90至105℃的温度下汽提来水解和除去在步骤(c),(d)或(e)中获得的溶液中的氨。
    • 9. 发明申请
    • Neutralization of isophorone nitrile synthesis products
    • 异佛尔酮腈合成产物的中和
    • US20060058544A1
    • 2006-03-16
    • US10539134
    • 2003-12-16
    • Alfred OftringGerold Braun
    • Alfred OftringGerold Braun
    • C07C253/08
    • C07C253/10C07C2601/14C07C255/46
    • The present invention relates to a process for preparing 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) by reacting isophorone with hydrogen cyanide in the presence of a base as a catalyst to obtain a crude isophoronenitrile product, and subsequently distilling the crude isophoronenitrile product, with the addition before distillation of at least one specific sulfonic acid or specific carboxylic acid. In addition, the present invention relates to the use of a specific sulfonic acid or of a specific carboxylic acid as a neutralizing agent before distillation of a crude isophoronenitrile product which has been obtained by reacting isophorone with hydrogen cyanide in the presence of a base as a catalyst, in order to avoid precipitates in the neutralization of the base used as a catalyst with an acid.
    • 本发明涉及一种在碱作催化剂存在下使异佛尔酮与氰化氢反应来制备3-氰基-3,5,5-三甲基环己酮(异佛尔酮)的方法,得到粗异烟酰腈产物,然后蒸馏粗产物 异佛尔酮腈产物,在蒸馏前加入至少一种特定的磺酸或特定的羧酸。 此外,本发明涉及在蒸馏前的异丙醇腈产物时使用特定的磺酸或特定羧酸作为中和剂,所述产物是通过在碱存在下将异佛尔酮与氰化氢反应而得到的 催化剂,以避免在用酸作为催化剂的碱的中和中沉淀。